


Not Your Average Cliche Love Story

by CelestialSilhouette



Category: Supernatural
Genre: 4+1, 5+1 Things, F/M, Falling In Love, Fluff and Angst, M/M, Meet the Family, Minor John Winchester/Mary Winchester, Past Character Death, Strangers to Lovers, Weddings, Well - Freeform, but who's counting
Language: English
Status: Completed
Published: 2020-11-05
Updated: 2020-11-05
Packaged: 2021-03-09 01:27:34
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,660
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27396454
Author URL: https://archiveofourown.org/users/CelestialSilhouette/pseuds/CelestialSilhouette
Summary: “Hey angel, how much did it hurt when you fell from heaven?” Jess asks, sliding down at the bar, next to the hottie with the long hair.He chokes on his beer. She thumps his back.“Don’t worry. I’m sure you’re not the first to do something like that.”He eyes her.It’s the start of something.(otherwise known as the 5 times sam and jess noticed really bad cliche and the one time they simply didn’t care)(the author is a sucker for 5+1 tropes, okay???)
Relationships: Castiel/Dean Winchester, Jessica Moore/Sam Winchester
Comments: 8
Kudos: 30





	Not Your Average Cliche Love Story

1.

“Hey angel, how much did it hurt when you fell from heaven?” Jess asks, sliding down at the bar, next to the hottie. 

He jerks to the side and chokes on his beer. She thumps his back, wincing. 

“Sorry, you okay man?”

He looks completely gobsmacked, as he stares at her face. She blinks. He blinks. 

“That’s cliche,” he blurts out, and immediately smacks his head. “That is not what I meant to say. Oh my god. I- I didn’t mean to say that I- I’m so sorry. Oh my god. I- wow. Okay.”

She giggles. “Smooth.”

“It’s been a while,” he admits, a small smile curling around his mouth.

“So… to save you the embarrassment, I’ll just give you my number then, okay?” He blinks.

“I- yeah, that’s probably for the best,” he lets out a short laugh.

“Well,” she sighs dramatically, “At least you’re cute.”

He eyes her. Smiles. “I’m Sam, by the way.”

“Jess. Nice to meet you Sam.”

“You too, Jess.”

It’s the start of something. 

2.

They’d been dating for a few months when Sam suddenly springs the family lunch on her. 

“You… uh… you want me to join your family lunch?”

“I mean,” Sam says, “the Novaks are going to be there too. They’re just… really close family friends...” he pauses again. “Well, okay. I guess family is right, after all.”

“Huh,” Jess says. She breathes in deeply. 

“Yeah. It’s been a few long and messy years, but we’re still family. Family don’t end in blood,” he says. Jess doesn’t know much about Sam’s past, but she knows how important family is to him. She knows from what she’s heard, and from Sam himself, that family is everything to him. And though he’s a perfect gentleman to all the women he dates, he also rarely takes them to meet his family. 

This, coincidentally, has absolutely nothing to do with the fact that her heart suddenly started to pound in her chest. 

“So, you’re inviting me to meet the family?”

He chuckles. “Yeah, we’re definitely there. 

“That’s cliche, babe” she says, patting him on the chest. Sam shakes his head, smiling. 

“That doesn’t count!”

She smiles as she leans down to kiss him. 

-

The diner is quaint and gives off a 50’s vibe. The lights are garishly bright and neon, and the tiles are checkered. Sam had explained that this was the place where John and Mary Winchester had met Becky and Chuck Novak. Quiet music filled the diner. 

Jess’ hands started getting sweaty. The doors open, and loud chatter drifts over to the table where Sam and Jess were at. Three people, a couple and a very short man, walks in. The man holds the door out dramatically, and says ‘for ‘m’lady’ as the woman walks in. She swats him on the arm.

“Hey guys!” Sam says. 

She gives a halfhearted wave. 

“So this is the famous Jess we’ve been hearing about non-stop for the past four months, huh?” the short man says. He’s holding a lollipop, and Jess instantly knows to be wary of him.

Sam’s face reddens. 

“Shut up, Gabe.”

Jess snickers. “That’s flattering, babe.”

Sam pouts. Gabe laughs at him, and Jess is thinking that her boyfriend is really starting to look like a pinched cow. Personally, she thinks it’s rather endearing. 

“It’s so nice to meet you,” Mary says. Jess recognizes her from the family pictures that Sam had shown her on their first date. 

“Likewise,” she says, smiling.

They sit down. A lot more people than Jess expected come over. She turns over to Sam, and whispers, “I have no idea who more than half of the people here are.”

Unfortunately, Gabe (Gabriel?) had been listening. He puts a hand on her shoulder and says, “Don’t worry kiddo. It’s pretty simple. My mom and dad, Becky and Chuck, are over there,” he points to a blonde woman with a beaming smile and a gruff looking genial man. 

“Beside them, is my brother, Jimmy and his lovely wife Amelia.”

Amelia is close enough to hear the conversation, and she bats away Gabe’s hand when he sticks it in her face. “Don’t you scare her off on her first meal!”

Gabe smirks. “Aww, darling, I didn’t scare you off, did I?”

“That’s because I punched you in the face.”

Gabe rolls his eyes. “It was a bonding experience.”

“Hey, your words, not mine. I wasn’t the one stuck with a black eye for a week,” Amelia smirks. “But anyways, nice to meet you Jess. Don’t let this lug get to you, okay?”

“I’ve been treating her like the lady she is! I’ve behaved perfectly and introduced her to the family” Gabe exclaims, mock-hurt. 

Jess shoots back. “If he wants to scare me off, he’s gonna have to try a lot harder than that.”

“See?” his grin widens. 

The door opens once moor, and air whooshes in. A man with blue eyes and a tan trenchcoat walks in, breathless. 

“And that,” Gabe points, “is Cassie!” 

“Ignore Gabriel,” the man says. “It’s Castiel.”

Amelia snorts. “Amen to that!” 

Gabe holds a hand to his heart dramatically. 

“I hear that you’re a psychologist, right?” Jimmy asks, leaning in. 

“I’m… I mean, I’m studying to become one,” Jess replies, lifting one shoulder weakly.

Gabe perks up at that. “You’re a shrink?” and barrels right through Jess’ indignant ‘that’s one way of putting it’ by exclaiming, “Ooo, try to guess what kind of food we are!”

“Like what we’re going to get?” Amelia asks, her eyebrows raised. 

“Potato, potahto.”

Jess says, “There is no way you aren’t getting a shit ton of dessert.”

Gabe nods in a conciliatory manner. “Go on, go on.”

“Jimmy seems like a… a laid back kind of guy, so something classic and simple. Like chicken nuggets and hashbrowns, and I remember you,” she says, pointing at Sam, “saying that Amelia likes fries.”

“Mmm hmm.”

“That’s cheating!” Gabe pouts, and then winks at Jess. “But you’re doing great. Continue.”

She rattles off each of the family members, giving a general response. Gabe’s mouth has dropped open by the time she reaches John. 

“Holy shit,” he whispers. 

“Holy shit,” he says, a little bit louder. “Is she or is she not completely accurate? How are you doing this?”

As any true Sherlock fan, Jess seizes the moment and opens her mouth to speak. 

“Wait!” he says, cutting her off, waggling his finger at her, “don’t you dare say ‘Elementary, my dear Watson.”

Jess shuts her mouth. Sam snickers. 

“I’m surprised you’ve even heard that phrase before,” Castiel says dryly. 

Gabe jumps up, clucking his tongue. “That’s rich coming from you. The only reason you know it is because Dean forced you to watch the TV show.”

Castiel blinks. “You… do know that it’s a book series, right?”

“But he never directly says that in the book!”

“What, like you haven’t ever searched a series up online?”

“No, I really haven’t. Why did you search it up online?”

“I… I was spoiling the ending,” Castiel says, his face flushing. 

Jess chokes. “You search the endings of books?”

“I know, right? This family, I swear!” Amelia says. 

“Look, it was a low point, alright? I knew that Sherlock fell to his death, leaving John alone, and there were still so many other books in the series. I simply… didn’t want to read that section.”

Gabe's mouth twitches downwards. “Okay. I guess you get a pass. But,” he whirls around and points at everyone else in the room, “None of you get that pass. Alright?”

“Sit down, Gabe,” Becky says. 

He sits down. 

“Alright, alright. But what about Cassie-”

“Castiel.”

“- I’ll bet that you wouldn’t be able to guess his order correctly.”

Jess scoffs. “Salad guy. Duh.”

Gabe’s entire body opens up, his back straightening and a wide grin breaking his face. “Incorrect! Cassie here, the monster, has always ordered a double bacon cheeseburger!”

She gapes. “Always?”

Castiel smiles awkwardly and his hands come up to the back of his neck. “Ah… yes. I do. Always.”

“What the fuck,” she whisperes, horrified. She turns to Sam, and says, “What the fuck!”

“Heard you the first time, babe.”

The waitress comes and serves the food. After a few inane comments about the food to Jess, everybody stops speaking. The only sounds are John and Chuck’s quiet commentary on the baseball game on the TV. Jess desperately tries to find a conversation topic.

“So…” Jess says slowly, dragging out the vowels, “So I didn’t get this earlier, but… um... Cas, are you a Winchester or Novak? Because when Gabe was introducing everyone I didn’t get...” her voice trails off. She gets the feeling that she just said something wrong. 

Castiel blinks, his entire posture looking akin to a deer in headlights. Sam stiffens behind her. Gabriel chokes. The whole table stops talking, stops eating, for god’s sake, it almost looks like they stop breathing.

It’s, to nobody’s surprise, Mary who breaks the silence.

“I guess it’s all a matter of perspective, right?”

Jimmy speaks up, a little too loud, a little too jovial, “Exactly! We all love Cas here, so to us, he’ll always be a Novak, but to the Winchesters, he’s one of them.”

“Not, though, that it matters. Cas is family. Everyone here is family,” John, out of all people, responds. 

Mary nods vigorously. Their lunch is markedly more awkward after that. 

3.

Later, Jess finds herself lying in bed with Sam, practically on top of him, ruminating about what went wrong. She burrows her head into his arms and groans. Sam’s face furrows with concern. 

“Hey, what’s wrong?”

Face still squished into Sam’s chest, she says, “I’m sorry I fucked up your family lunch.”

“What?” Sam asks, surprised. “You didn’t ruin anything! It actually went a lot better than expected.”

Jess lifts her face for the sole purpose of staring Sam down. He laughs. 

“Okay, okay, so the end could have gone a little better. But trust me, they like you. They know that you’re special. Besides, I like you, right?”

“Sam,” Jess sighs, “That’s not helpful.”

“But it’s the most important part, right?”

“That doesn’t mean I don’t want your family to like me!”

Sam bites his lips. “Look… Our families have been close friends for a long time. The Novaks have been our neighbors for as long as I can remember. The thing is… Cas is Jimmy and Gabe’s brother, and-”

“So wouldn’t that make him a Novak? What, did he cause some big family scandal” she says, drawing out the words, “and they disowned him for a bit? Because, from what you’ve told me about Gabriel, it seems unlikely that they’d do that.”

“No, that’s not-”

“Or is he gay?” she suddenly sits up. “Are they homophobic? Are you homophobic?”

“That’s got nothing to do with-”

“Wait, but then how is he a Winchester? Oh! I get it! You guys took him in when he ran away, didn’t you?”

“You’re confusing the plot of a cliche chick flick with real life again-”

“And then you guys adopted him and helped bring their family back together! That’s so sweet!”

“Jess!” Sam breaks her train of thoughts. 

She shuts up. His shoulders are shaking with laughter. 

“That’s not at all what happened. Cas is bi, and,” he pauses, “Yeah, okay, the Novaks are religious, but they were also extremely supportive. They’re good people, they’d never kick Cas out.”

Jess’ face reddens, as she slowly lays back down onto his arms. “Oh… I see. I- Sorry, I have no idea how I came to that conclusion, I-”

“Seriously, don’t be. I’m sure that you wouldn’t have been the first person to come to that conclusion. But… no, that’s not what happened,” Sam pauses. 

“Cas is my brother’s widower.”

“Oh,” Jess whispers. She hunches in on herself, and doesn’t speak. She doesn’t trust herself to. 

Sam smiles, albeit sadly. “Yeah. They were best friends throughout childhood. You couldn’t have found one without the other -- they were attached at the hip. Nobody was surprised when they started dating, and eventually married each other.”

“Oh,” Jess repeats herself. Her face flushes and she finds it hard to meet Sam’s eyes. 

“Yeah. Cas never really got over him. I don’t think Cas will, either. You know, you were right to be surprised at the diner, when Cas got that burger. It’s not really his thing. But my brother loved his burgers.”

“Dean, right?”

Sam blinks. “What?”

“You’re brother’s name is Dean, right?”

Sam nods slowly. 

“He sounds like an amazing man. I wish I could’ve met him.”

It’s quiet for such a long time, that Jess thinks Sam fell asleep, before he replies, “I wish you could’ve met him too.”

4.

The next ‘meet-the-family’ moment is at the cemetery. Jess is standing in front of a polished granite gravestone, with the words ‘Dean Winchester’ inscribed on the top, and ‘1/24/1979 - 12/24/2009’ written in smaller letters on the bottom. 

Sam is silently staring at the gravestone next to her. A light breeze wafts over them, bringing colorful autumn leaves near them. She doesn’t know what to say. 

She swallows. Bites her lip. Sucks in a breath. “Hi Dean,” she says. 

There is no response. Of course not, Dean’s dead and six feet under. But this is Sam’s brother, this is important. 

“I’m Jess. Jessica Lee Moore. Um… I’m your brother’s girlfriend.”

Sam’s staring at her now, but he’s still not saying a word. She breathes in another shaky breath, and her heart pounds. 

“I just thought you should know… I really really like him. And I know, or, well, I’ve heard, that you were really protective over Sam when you were alive. So I wanted to tell you… I... I think I love him. I really do. We’re in it for the long haul. Um… I just wanted to say… thank you. For, you know, caring for Sam, helping him become the person he is today. But you rest, okay? Because I’m gonna take care of him now.”

Sam’s crying, but he’s still clutching her hands so so tightly, and she must be doing something right, because he pulls her in for a hug and doesn’t let go for a long time. They clutch each other tightly. 

“Cliche,” he whispers wetly. They laugh in between kisses. 

They let go after a while, and start walking back to the car, hand in hand. 

From the distance, Jess can see a lone figure walking to where they just left. It takes her a while to notice that it’s Castiel, and she realizes that he must have made the decision to leave them alone, to wait until they were gone, before visiting Dean. 

He must have seen them hugging each other, and kissing each other in front of the grave. He must have seen them caring for each other, and chances are, he might have even heard her declaration of love to Sam. She can see Castiel kneeling down, collapsing on himself, his shoulders hunching over and his too-big trenchcoat making his body look even smaller than it already is. He clutches the ring attached to the chain on his neck tightly, tightly, and his face crumbles as he cries. 

Her heart breaks for him. 

+1.

She cried when Sam proposed. They spent a long time planning the wedding, but when the big day finally comes, they’re both prepared. 

The tent is completely decked out, with silver and gold streamers wrapping around the whole place. The walkway is decorated in rose petals, similar to the ones on the beach when Sam proposed. It’s extravagant and luxurious and everything Jess never thought she would have. Their entire family is there, not a single face missing. 

Jess looks over at them nervously as she slowly walks to Sam, where he and his groomsmen were. His smile is radiant, and he looks wonderful. Her lips curl up when she sees him, and she knows that she must look like a lovesick puppy. 

She isn’t paying attention to the officiate, she’s too busy staring at Sam, so when she’s supposed to say her vows, she doesn’t even notice until she realizes everything is too quiet. She laughs, and her heart is pounding, but she isn’t nervous because this just feels so right. There is no world where this wasn’t made to be, and she says so in her vow.

“It feels like I’ve just loved you my whole life. I can’t imagine a world without you, and I hope I never have to. 

Sam, baby, I love you more than I love the sky and the stars and the world itself. I love you so much that I don’t even know how to begin to show you just how much I love you. It’s overwhelming and incandescent and beautiful. I don’t know how to show you just the extent of how much I love you, so here’s what I promise to do. I promise to hug you and kiss you and tell you I love you every day. I promise to let you keep your hair, let you eat your rabbit food, and let you say all of your stupid cliches, and I promise to never ever let you go.”

Sam’s crying, tears are streaming down his face. She barely hears his vow in response, but she feels him, and when they kiss it’s the most perfect feeling in the world. It’s sweet and long and delicate but it’s also so so much and she doesn’t think she’ll ever stop, she’ll just pause this moment and keep it on hold forever and ever and that would be just fine. 

After their first dance, they simply sway in each other’s arms for a long time. 

John and Mary find them a while later, their hands joined. 

John grins. “Jess, you look lovely tonight.”

“Thank you. I- thank you,” Jess stammers. It’s been years, and she still gets flustered around her father-in-law (holy shit!). 

What? John’s terrifying!

“Well, Sam, you wouldn’t happen to be too busy to share a dance with your mother, would you?” Mary asks, her eyes twinkling. 

“Of course,” Sam says, and with one last kiss on Jess’ cheeks, he disengages their arms and starts dancing with his mother. 

John sighs. “I’m just glad that both of my sons had the chance to be happy in their lives.”

Jess doesn’t say anything. She doesn’t know what to say. 

“Thank you. For making Sam so happy. I only wish…” he pauses. “But that isn’t a conversation suitable for today. This should be a happy day. And yet…”

They both turn around, and look in the same direction. Cas is sitting alone, hunched over. He’s holding a glass of wine in his hand like it’s the only thing that can save him. He looks miserable. 

“I know. I’m sorry.”

John looks at her incredulously. “Sorry? What do you have to be sorry for? You and Cas… you two make… made my sons so happy. I can’t thank the two of you enough for that. I… you should know that I am proud to be able to call you my daughter.”

She nods, tears prickling at the edge of her eyes.

“Thank you.”

The song ends. John smiles again, pats her on the back, and walks away. 

She walks aimlessly for a while. She’s stopped and congratulated by a few distant family members and family friends but before she knows it, she’s standing in front of a table. She sits down.

“Hi Cas.”

He looks up sharply and breathes in. “Hello Jess. You… ah… you were wonderful tonight. You and Sam are perfect together,” he says. He tries to sound cheerful, but it just comes out flat. 

“I’m sorry,” she says simply. 

His careful facade falls apart right in front of her, and she wraps her arms around him as he sobs. She rocks him back and forth and they stay like that for a while. 

“I- I’m so sorry, this is your wedding, I’ve ruined your dress, I-” he rambles. 

“Hush. Cas, you… It’s okay to be sad. You know that right?”

“It’s your wedding.”

“I know. But you can be happy for us and sad for yourself.”

He nods. They both stay silent, watching everybody dancing and talking with each other. Sam looks at her from the dance floor, while dancing with her mother. His face is concerned, but she shakes her head, smiling at him. His face softens. 

She’s got this handled. 

“You know, I’m proud to be your sister.”

Castiel glances at her, touches her face, and smiles weakly. “I am proud to be your brother as well.”

She stands up, and kisses him on the cheeks. Then, she makes her way over to Sam, and finds her way into his arms again. 

“Everything alright?” he asks. 

“Yeah. Everything’s alright.”

Sam sighs. “You know, when I first thought about getting married, I always thought that Dean was going to be next to me. He would be my best man, and tell embarrassing stories that would make me want to hide for the rest of eternity. I guess… it never occurred to me that he might not be here. God, it never even occurred to me that I would be older than him someday. 

“When I first started dating, he would scare away all the girls who he thought ‘weren’t good enough for me’”, he makes a face and continues, “But you know what? I see you every day, and I think that he would have loved you.”

She thinks she’s going to cry for the hundredth time that night. She thinks that she can see the sun and the stars and the whole fucking universe in Sam’s eyes.

As they dance in each other’s arms, utterly content and utterly in love, she thinks that this is really the start of something. 

It’s the start of the rest of their lives.

**Author's Note:**

> I’d like to believe that supernatural elements do exist in this story and Dean comes back as a ghost just to fuck with everyone. And to kiss Cas. That is my hot take on this, thank you for reading. 
> 
> I don’t know why I wrote this, I just made myself sad.


End file.
